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[ CAS No. 94-05-3 ] {[proInfo.proName]}

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Chemical Structure| 94-05-3

Chemical Structure| 94-05-3

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Quality Control of [ 94-05-3 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 94-05-3 ]

CAS No. :	94-05-3	MDL No. :	MFCD00009136
Formula :	C₈H₁₁NO₃	Boiling Point :	-
Linear Structure Formula :	(NC)(COOC₂H₅)CCHOC₂H₅	InChI Key :	KTMGNAIGXYODKQ-VOTSOKGWSA-N
M.W :	169.18	Pubchem ID :	1715183
Synonyms :

Safety of [ 94-05-3 ]

Signal Word:	Danger	Class:	9
Precautionary Statements:	P264-P261-P270-P271-P272-P280-P285-P305+P351+P338-P310-P302+P352-P304+P340-P330-P342+P311-P362+P364-P403+P233-P501	UN#:	3335
Hazard Statements:	H302-H315-H317-H318-H334-H335	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 94-05-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 94-05-3 ]
Downstream synthetic route of [ 94-05-3 ]

[ 94-05-3 ] Synthesis Path-Upstream 1~4

1
[ 2986-19-8 ]
[ 94-05-3 ]
[ 89487-99-0 ]

Yield	Reaction Conditions	Operation in experiment
65%	With potassium carbonate In ethanol for 48 h; Heating / reflux	2-Methyl-2-thiopseudourea (5 mmol) and ethyl ethoxymethylenecyanoacetate (5 mmol) were dissolved in 20 ml EtOH. To this was added K₂CO₃(10 mmol). After the mixture was refluxed for 48 h, it was cooled to room temperature and filtered. The solvent was concentrated in vacuo and purified by column chromatography to give 4-hydroxy-2-(methylthio) pyrimidine-5-carbonitrile in a yield of 65percent.

Reference： [1] Patent: US2008/255172, 2008, A1, . Location in patent: Page/Page column 70

2
[ 94-05-3 ]
[ 89487-99-0 ]

Reference： [1] Patent: US2009/270389, 2009, A1, . Location in patent: Page/Page column 43

3
[ 14527-26-5 ]
[ 94-05-3 ]
[ 89487-99-0 ]

Reference： [1] Patent: US2003/158218, 2003, A1,

4
[ 6829-40-9 ]
[ 94-05-3 ]
[ 853058-40-9 ]

Reference： [1] Patent: US6693193, 2004, B1, . Location in patent: Page column 14
[2] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 1, p. 218 - 222

[ 94-05-3 ] Synthesis Path-Downstream 1~12

1
[ 120-35-4 ]
[ 94-05-3 ]
<(2-Methoxy-5-phenylcarbamoyl-anilino)-methylen>-cyanessigsaeureethylester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,1964,vol. 7,p. 68 - 72

2
[ 57508-48-2 ]
[ 94-05-3 ]
[ 130484-63-8 ]

Reference： [1]Journal of Heterocyclic Chemistry,1990,vol. 27,p. 1143 - 1151

3
[ 371-14-2 ]
[ 94-05-3 ]
[ 138907-68-3 ]

Reference： [1]Journal of Medicinal Chemistry,2006,vol. 49,p. 1562 - 1575
[2]Patent: EP1176140,2002,A1 .Location in patent: Page 45 - 46

4
[ 823-85-8 ]
[ 94-05-3 ]
[ 138907-68-3 ]

Yield	Reaction Conditions	Operation in experiment
72%	With triethylamine; In ethanol; for 2.5h;Heating / reflux;	Ethyl(ethoxymethylene)cyanoacetate (20.80 g, 123 mmol) and triethylamine (17.1 ml_, 123 mmol) were added to a solution of 4-fluorophenylhydrazine hydrochloride (20.00 g, 123 mmol). The reaction mixture was refluxed for 2.5 hours and allowed to cool to room temperature. A solid was collected by filtration, washed with small amounts of ethanol and EPO <DP n="37"/>heptane and allowed to dry under reduced pressure to afford the title compound as a beige solid (22.18 g, 72 % yield). m/z 250 [M+H]+. 1H NMR (300 MHz, CDCI3) 7.80 (1 H, s), 7.58-7.51 (2H, m), 7.27 (2H, m), 5.27 (2H, br s), 4.33 (2H1 q, J=7.2 Hz), 1.39 (2H, t, J=7.2 Hz).
65%	With triethylamine; In ethanol; at 20 - 80℃; for 8h;	General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+].
	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	Intermediate 8: Ethyl 5-amino-1-(4-fluorophenyl)-1 H-pyrazole-4-carboxvlate. To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5hr. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid. 1 H NMR (400 MHz, DMSOd6) deltappm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).

	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	Intermediate 8; Ethyl 5-amiotano-1-(4-fluorophenyl)-1/-/-pyrazole-4-carboxylateTo a stirred suspension of 4-fluorophenylhydraziotane hydrochloride (9 76g, 60mmol) in ethanol (250ml) was added triethylamine (9 2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10 15g, 60mmol) The solution was heated at reflux temperature for 3 5 hours The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12 1g) as an off white solid1H NMR (400 MHz, DMSO-d6) delta ppm 7 70 (s, 1 H) 7 55 (s, J=5 0 Hz, 2H) 7 34 - 7 41 (m, 2 H) 6 34 (br s , 2H) 4 21 (q, J=I 0, 7 0 Hz, 2H) 1 26 (t, J=I 0 Hz, 3H)
	With triethylamine; In ethanol; for 3.5h;Heating / reflux;	To a stirred suspension of 4-fluorophenylhydrazine hydrochloride (9.76g, 60mmol) in ethanol (250ml) was added triethylamine (9.2ml, 62mmol) and to the resulting amber solution was added ethyl 2-cyano-3-ethoxyacrylate (10.15g, 60mmol). The solution was heated at reflux temperature for 3.5 hours. The solution was allowed to cool to room temperature and after standing overnight the resultant solid was filtered off, washed with small amount of ethanol and then ether before being dried under vacuum to give the title compound (12.1 g) as an off white solid.1H NMR (400 MHz, DMSO-cfe) delta ppm 7.70 (s, 1 H) 7.55 (s, J=5.0 Hz, 2 H) 7.34 - 7.41 (m, 2 H) 6.34 (br. s., 2 H) 4.21 (q, J=7.0, 7.0 Hz, 2 H) 1.26 (t, J=7.0 Hz, 3 H).
	With sodium acetate; In ethanol; at 95℃; for 3.5h;	(i) Ethyl-2-cyano-3-(ethyloxy)-2-propenoate (5.0 g, 29.56 mmol), (4- fluorophenyl)hydrazine hydrochloride (4.81 g, 29.56 mmol) and sodium acetate (2.43 g, 29.56 mmol) were dissolved in ethanol (100 ml) and heated for 3.5 hrs at 95C. The mixture was then cooled to room temperature and diluted with dichloromethane (-150 ml) and water (50 ml). The organic layer was separated using a hydrophobic <n="105"/>frit, dried over anhydrous sodium sulphate, filtered and to give ethyl 5-amino-1-(4- fluorophenyl)-1 H-pyrazole-4-carboxylate (6.83 g) as an orange solid. This was used in the next step without further purification.

Reference： [1]Patent: WO2008/53136,2008,A1 .Location in patent: Page/Page column 35-36
[2]Tetrahedron,2017,vol. 73,p. 5959 - 5973
[3]Patent: WO2008/74814,2008,A1 .Location in patent: Page/Page column 55
[4]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4724 - 4728
[5]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 1680 - 1684
[6]Patent: WO2008/777,2008,A2 .Location in patent: Page/Page column 58
[7]Patent: WO2007/144327,2007,A2 .Location in patent: Page/Page column 70
[8]Patent: WO2008/138876,2008,A1 .Location in patent: Page/Page column 103-104

5
[ 168268-00-6 ]
[ 94-05-3 ]
6-benzyloxy-7-fluoro-4-oxo-1,4-dihydro-3-quinolinecarbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		A mixture of <strong>[168268-00-6]4-benzyloxy-3-fluoroaniline</strong> (6.06 g, 27.9 mmol) (US 5,622, 967) and ethyl (ethoxymethylene) cyanoacetate (5.08 g, 30.0 mmol) was heated at 120C for 45 minutes then cooled to room temperature. This solid was added in portions to a 3: 1 mixture of diphenyl ether: biphenyl at 245 C. This mixture was heated at 245C for 3 hours then cooled and the solids were collected by filtration, washing with hexane and diethyl ether to provide 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4- dihydro-3-quinolinecarbonitrile, mp >250C. MS 293.1 (M-H) -
	at 120℃; for 0.75h;	A mixture of <strong>[168268-00-6]4-benzyloxy-3-fluoroaniline</strong> (6.06 g, 27.9 mmol) (U.S. Pat. No. 5,622,967) and ethyl (ethoxymethylene)cyanoacetate (5.08 g, 30.0 mmol) is heated at 120 C. for 45 minutes then cooled to room temperature. This solid is added in portions to a 3:1 mixture of diphenyl ether:biphenyl at 245 C. This mixture is heated at 245 C. for 3 hours then cooled and the solids are collected by filtration, washing with hexane and diethyl ether to provides 2.60 g of 6-benzyloxy-7-fluoro-4-oxo-1, 4-dihydro-3-quinolinecarbonitrile, mp>250 C. [0198] MS 293.1 (M-H)-

Reference： [1]Patent: WO2005/47259,2005,A1 .Location in patent: Page/Page column 11; 22-23
[2]Patent: US2003/212276,2003,A1 .Location in patent: Page/Page column 12

6
[ 94-05-3 ]
[ 138907-68-3 ]

Yield	Reaction Conditions	Operation in experiment
74%	With potassium carbonate; In ethanol; water;	PREPARATION A Ethyl-5-Amino-1-(4-fluorophenyl)-1H-pyrazole-4-carboxylate A stirred mixture of 11.38 g (70.0 mmole) of a commercially available sample of 4-fluorophenylhydrazine hydrochloride, 11.84 g (70.0 mmole) of ethyl (ethoxymethylene)cyanoacetate and 9.67 g (70.0 mmole) of potassium carbonate in 100 ml of ethanol was refluxed overnight and then treated with 300 ml of water. The precipitate was filtered and dried in vacuo to furnish 12.87 g (74% yield) of pale yellow crystalline solid. The sample was recrystallized from ethanol m.p. 151-2 C. Analysis: Calculated for C12 H12 FN3 O2: C, 57.82; H, 4.85; N, 16.86%. Found: C, 57.82; H, 4.78; N, 16.79%.

Reference： [1]Patent: US5064851,1991,A

7
[ 33906-30-8 ]
[ 94-05-3 ]
[ 25468-51-3 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium acetate; In water; N,N-dimethyl-formamide;	EXAMPLE 1 A solution of 50 g. (0.27 mole) of <strong>[33906-30-8]2-hydrazinobenzoic acid hydrochloride</strong> [Pfanntiel et al., Ber. 75B, 1096-1107 (1942)], 45 g. (0.26 mole) of ethyl ethoxymethylenecyanoacetate and 26.4 g. (0.32 mole) of sodium acetate in 330 ml. of DMF was heated to 140 C., then cooled to ambient temperature, diluted with 130 ml. of water and chilled. The solid which separated was collected, washed with water, then with ethanol, then with diethyl ether and dried to give 62.6 g. of ethyl 4,5-dihydro-5-oxopyrazolo[1,5-a]quinazoline-3-carboxylate, m.p. 203-205 C.

Reference： [1]Patent: US4105766,1978,A

8
[ 30616-38-7 ]
[ 94-05-3 ]
[ 1175535-56-4 ]

Reference： [1]Journal of Chemical Research,2008,p. 715 - 718

9
[ 33906-30-8 ]
[ 94-05-3 ]
[ 25468-51-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2009,vol. 19,p. 4196 - 4200

10
[ 60-34-4 ]
[ 94-05-3 ]
[ 21230-43-3 ]

Reference： [1]Organic Letters,2015,vol. 17,p. 2964 - 2967

11
[ 637-60-5 ]
[ 94-05-3 ]
[ 15001-11-3 ]

Yield	Reaction Conditions	Operation in experiment
85%	With triethylamine; In ethanol; at 20 - 80℃; for 8.0h;	General procedure: To ethyl 2-cyano-3-ethoxyacrylate (2.00 g, 11.8 mmol) and 4-methoxyphenyl hydrazine hydrochloride (2.06 g, 11.8 mmol) in ethanol (75 mL) at room temperature was added triethylamine (1.65 mL, 11.8 mmol). The mixture was stirred at 80 C for 8 h. After cooling the reaction mixture to room temperature, ethanol was removed in vacuo and the residue was partitioned between ethyl acetate and water. The organic layer was dried over magnesium sulfate. The solvent was evaporated in vacuo and the residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1) to give the desired product 2b (2.42 g, 78 %). 1H NMR (300 MHz, CDCl3): delta=7.76 (s, 1H), 7.42 (d, J=6.9Hz, 2H), 7.01 (d, J=6.9Hz, 2H), 5.19 (br s, 2H), 4.30 (q, J=7.1Hz, 2H), 3.82 (s, 3H), 1.36 (t, J=7.1Hz, 3H) ppm; MS (ESI): m/z: 262 [M+H+].

Reference： [1]Tetrahedron,2017,vol. 73,p. 5959 - 5973

12
[ 1583-59-1 ]
[ 94-05-3 ]
ethyl 2-cyano-3-(2,2-difluoro-1,3-benzodioxol-4-yl)acrylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
43 g		(2) Cool down to -50 C,Under the protection of nitrogen,Add 100 ml of n-hexane and 90 ml to a 500 ml four-necked flask equipped with a stirrer and a condenser.(0.2 mol) t-butyl lithium solution,Then <strong>[1583-59-1]2,2-difluorobenzo-1,3 dioxol</strong>ane 32g was added dropwise(0.2mol)(Drip in 0.5~2h),Insulation reaction for 4h,After the completion of the heat preservation, 100 ml of 47.6 g (0.28 mol) of ethyl ethoxymethylene cyanoacetate was added dropwise over 3 hours.The tetrahydrofuran solution was then incubated for 1 h, warmed to room temperature for 3 h, and finally neutralized to neutral with dilute hydrochloric acid.100ml*2 ethyl acetate extraction,Dry the organic phase with magnesium sulfate,Concentrated under reduced pressure,Filter drydryGet 2-cyano-3-(2,2-difluorobenzo-1,3-dioxole-4-yl)-2-acrylate 43g

Reference： [1]Patent: CN103497180,2016,B .Location in patent: Paragraph 0045; 0055; 0058; 0089

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Technical Information

? Acyl Group Substitution ? Blaise Reaction ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Complex Metal Hydride Reductions ? Ester Cleavage ? Heat of Combustion ? Hydride Reductions ? Preparation of Aldehydes and Ketones ? Preparation of Amines ? Reactions with Organometallic Reagents ? Ritter Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Thorpe-Ziegler Reaction

Historical Records

Pharmaceutical Intermediates of
[ 94-05-3 ]

Bosutinib Intermediates

[ 380844-49-5 ]

7-(3-Chloropropoxy)-4-((2,4-dichloro-5-methoxyphenyl)amino)-6-methoxyquinoline-3-carbonitrile

[ 846023-24-3 ]

2-Cyano-N-(2,4-dichloro-5-methoxyphenyl)acetamide

[ 5317-33-9 ]

3-(4-Methylpiperazin-1-yl)propan-1-ol

[ 98446-49-2 ]

2,4-Dichloro-5-methoxyaniline

[ 87-13-8 ]

Diethyl 2-(ethoxymethylene)malonate

Neratinib Related Intermediates

[ 848133-75-5 ]

N-(3-Cyano-7-ethoxy-4-hydroxyquinolin-6-yl)acetamide

[ 179687-79-7 ]

2-((2-Chloro-4-nitrophenoxy)methyl)pyridine

[ 619-08-9 ]

2-Chloro-4-nitrophenol

[ 848133-76-6 ]

N-(4-Chloro-3-cyano-7-ethoxy-6-quinolinyl)acetamide

[ 524955-09-7 ]

3-Chloro-4-(pyridin-2-ylmethoxy)aniline

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P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Ghs Hazard Statements

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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