14191-95-8

Basic information

• Product Name: 4-Hydroxybenzyl cyanide
• Synonyms: Acetonitrile, (p-hydroxyphenyl)-;Benzeneacetonitrile, 4-hydroxy-;p-Hydroxyphenylacetonitrile;p-Hydroxybenzacetonitrile;4-HydroxybenzylCyanide98+%;4-Hydroxybenzyl;4-HYDROXY BENZYLCYARIDE;PARA-HYDROXYPHENYLACETONITRILE
• CAS NO: 14191-95-8
• Molecular Formula: C₈H₇NO
• Molecular Weight: 133.15
• EINECS: 238-046-0
• Product Categories: Aromatic Nitriles;Aromatics;Inhibitors
• Mol File: 14191-95-8.mol
• Article Data: 28

Chemical Properties

• Melting Point: 67-70 °C(lit.)
• Boiling Point: 330 °C756 mm Hg(lit.)
• Flash Point: 178 °C
• Appearance: light brown solid
• Density: 1.1475 (rough estimate)
• Vapor Pressure: 8.91E-05mmHg at 25°C
• Refractive Index: 1.5260 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: Chloroform, DMSO, Methanol (Slightly)
• PKA: 9.63±0.13(Predicted)
• Water Solubility: slightly soluble
• BRN: 1934470
• CAS DataBase Reference: 4-Hydroxybenzyl cyanide(CAS DataBase Reference)
• NIST Chemistry Reference: 4-Hydroxybenzyl cyanide(14191-95-8)
• EPA Substance Registry System: 4-Hydroxybenzyl cyanide(14191-95-8)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38
• Safety Statements: 36/37-36/37/39-26
• RIDADR: 3439
• WGK Germany: 3
• RTECS: AM0530000
• HazardClass: 6.1
• PackingGroup: III
• Hazardous Substances Data: 14191-95-8(Hazardous Substances Data)

Usage

Chemical Properties

Light Brown Solid

Uses

4-Hydroxyphenylacetonitrile (cas# 14191-95-8) is a compound useful in organic synthesis.

Definition

ChEBI: A hydroxynitrile that is phenylacetonitrile substituted by a hydroxy group at position 4.

InChI:InChI=1/C8H7NO/c9-6-5-7-1-3-8(10)4-2-7/h1-4,10H,5H2

Synthetic route

2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With tetrachlorosilane; borontrifluoride acetic acid; lithium iodide In toluene; acetonitrile at 70℃; for 2h;	98%

Methyl formate (107-31-3) + (4-hydroxyphenyl)methanol (623-05-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With sulfuric acid In methanol; dichloromethane; water	96%

p-methoxybenzylnitrile (104-47-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Stage #1: p-methoxybenzylnitrile With aluminum (III) chloride In toluene at 20 - 70℃; for 4.33 - 6.5h; Stage #2: With hydrogenchloride; water In toluene at 20℃;	95.41%
Stage #1: p-methoxybenzylnitrile With aluminium trichloride In toluene at 70℃; Stage #2: With hydrogenchloride; water at 20℃; Further stages.;	84%
With 1-butylpyridinium bromide at 100℃; Microwave irradiation; Neat (no solvent);	84%

(4-hydroxyphenyl)methanol (623-05-2) + formic acid ethyl ester (109-94-4) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
In ethanol	94%

4-Bromophenylacetonitrile (16532-79-9) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With tris(6,6'-diamino-2,2'-bipyridine); 4,4-diphenyl-1,3,5,7,8-pentamethyl-2,6-diethyl-4-bora-3a,4a-diaza-s-indacene; Br2Ni*3H2O; water; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide; acetonitrile at 20℃; for 24h; Glovebox; Irradiation; Inert atmosphere;	89%

4-(cyanomethyl)phenylboronic acid (91983-26-5) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With oxygen; triethylamine In acetonitrile under 760.051 Torr; for 24h; Irradiation; Green chemistry;	85%

Triethoxysilane (998-30-1) + 2-(4-hydroxyphenyl)acetamide (17194-82-0) → 4-cyanomethylphenol (14191-95-8) + C12H30O7Si2

Conditions	Yield
With C22H48FeOP4 In tetrahydrofuran at 60℃; for 24h; Inert atmosphere; Schlenk technique;	A 85% B n/a

2-(4-hydroxyphenyl)acetamide (17194-82-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With Triethoxysilane; C43H50FeP4Si; zinc dibromide In tetrahydrofuran at 40℃; for 30h; Schlenk technique;	82%
With diphenylsilane; FeH(PMe3)2(SiPh(NCH2PPh2)2C6H4) In tetrahydrofuran at 70℃; for 24h; Schlenk technique; Inert atmosphere;	55%

N-(hydroxyphenyl)glycine (122-87-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With sodium hydroxide In water; N,N-dimethyl-formamide	80%

sodium cyanide (773837-37-9) + (4-hydroxyphenyl)methanol (623-05-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
In N,N-dimethyl-formamide	67%
In N,N-dimethyl-formamide at 120℃; for 26h; Inert atmosphere;	546 mg
With tetrabutylammomium bromide

sodium cyanide (773837-37-9) + 4-methoxy-phenol (150-76-5) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
In N,N-dimethyl-formamide at 130℃; for 24h;	65%

L-Tyr-NH2 (4985-46-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With potassium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 0 - 5℃; for 1.5h;	61%

L-tyrosine (60-18-4) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With potassium hydroxide; [bis(acetoxy)iodo]benzene In methanol at 0 - 5℃; for 1.5h;	52%
With hydrogenchloride; sode de l'acide trichloroisocyanurique In water for 3h;

2-acetyl-3-(4-methoxyphenyl)isoxazol-5(2H)-one (267877-40-7) → 4-cyanomethylphenol (14191-95-8) + 4-acetaminophenol (103-90-2) + 4-cyanophenol (767-00-0) + 4-(2-methyloxazol-4-yl)phenol

Conditions	Yield
at 750℃; Product distribution; Further Variations:; Temperatures; Rearrangement; decomposition;	A 25% B 7% C 45% D 23%

4-hydroxybenzyl chloride (35421-08-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
In acetonitrile	45%
In acetonitrile	45%

p-aminophenylacetonitrile (3544-25-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With sodium nitrite

2-(hydroxyimino)-3-(4-hydroxyphenyl)propanoic acid (56401-28-6) + acetic anhydride (108-24-7) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Erwaermen des Reaktionsprodukts mit wss. NaOH;

4-hydroxybenzyl chloride (35421-08-0) + sodium cyanide (143-33-9) → 4-cyanomethylphenol (14191-95-8)

sinalbin → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With water; silver nitrate man behandelt den Niederschlag in waessr. Suspension mit H2S;

(S)-2-[(S)-2-Amino-3-(4-hydroxy-phenyl)-propionylamino]-3-(4-hydroxy-phenyl)-propionic acid (1050-28-8) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: KOH, PhI(OAc)2 / 1.5 h / 0 - 5 °C 2: 52 percent / PhI(OAc)2, KOH / methanol / 1.5 h / 0 - 5 °C View Scheme

p-cresol (106-44-5) + n-C3H7X → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Multi-step reaction with 5 steps 2: PCl3, PhCONH2, (PhCO)2O2, SO2Cl2 / 135 °C View Scheme

p-chloromethyl-phenyl chloroformate (15451-04-4) → 4-cyanomethylphenol (14191-95-8)

-chlorid (61661-14-1) → 4-cyanomethylphenol (14191-95-8)

p-tolyl chloroformate (937-62-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Multi-step reaction with 4 steps 1: PCl3, PhCONH2, (PhCO)2O2, SO2Cl2 / 135 °C View Scheme

propyl methanoate (110-74-7) + (4-hydroxyphenyl)methanol (623-05-2) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With formic acid In N,N-dimethyl-formamide

(4-hydroxyphenyl)methanol (623-05-2) → 4-cyanomethylphenol (14191-95-8)

4-hydroxyphenylacetonitrile 4-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside (1252085-64-5) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
With β-glucosidase from almonds; water at 37℃; for 4h; pH=5; McIlvaine buffer; Enzymatic reaction;

4-hydroxy-benzaldehyde (123-08-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Multi-step reaction with 2 steps 1: hydrogen 2: tetrabutylammomium bromide View Scheme

benzamide (55-21-0) → 4-cyanomethylphenol (14191-95-8)

Conditions	Yield
Multi-step reaction with 3 steps 1: sulfuryl dichloride; dibenzoyl peroxide 2: methanol; acetonitrile 3: acetonitrile View Scheme

4-cyanomethylphenol (14191-95-8) + isopropyl bromide (75-26-3) → 2-[4-(propan-2-yloxy)phenyl]acetonitrile (50690-53-4)

Conditions	Yield
With potassium carbonate In dimethyl sulfoxide	99%
With sodium hydride In N,N-dimethyl-formamide at 60℃;	85%

4-cyanomethylphenol (14191-95-8) → p-{[(hydroxy)imino]-2-aminoethyl}phenol (58484-76-7)

Conditions	Yield
With hydroxylamine hydrochloride; potassium carbonate In ethanol for 4h; Heating;	99%

4-cyanomethylphenol (14191-95-8) + ethyl bromoacetate (105-36-2) → C12H13NO3 (1016887-21-0)

Conditions	Yield
With potassium carbonate; sodium iodide In acetonitrile at 20℃; for 24h; Reflux;	99%

methanol (67-56-1) + 4-cyanomethylphenol (14191-95-8) → methyl-2-(4-hydroxyphenyl)acetimidate hydrochloride

Conditions	Yield
With acetyl chloride at -20 - 20℃; Inert atmosphere;	99%

4-cyanomethylphenol (14191-95-8) + acetic anhydride (108-24-7) → O-acetyl-4-hydroxyphenylacetonitrile (67741-16-6)

Conditions	Yield
In pyridine at 120℃; for 4h;	98.5%
With pyridine at 120℃; for 4h; Inert atmosphere;	98%
With pyridine at 120℃; for 4h; Inert atmosphere;	98%

4-cyanomethylphenol (14191-95-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-(tert-butyldimethylsilyloxy)-phenyl-acetonitrile (167263-57-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃; for 3h;	98%
With 1H-imidazole; dmap In dichloromethane at 0℃; for 8.16667h;	97%
With 1H-imidazole; dmap In DMF (N,N-dimethyl-formamide) at 20℃; for 16h;

4-cyanomethylphenol (14191-95-8) → 2-(4-hydroxyphenyl)acetamide (17194-82-0)

Conditions	Yield
With bis(dimethylphosphinous acid-kP)dimethylphosphinyl-kP-hydridoplatinum(II) In ethanol; water for 18h; Reflux;	98%
Multi-step reaction with 3 steps 1: KOH-solution 2: HCl 3: aqueous ammonia / 105 °C View Scheme

1H-imidazole (288-32-4) + 4-cyanomethylphenol (14191-95-8) + tert-butyldimethylsilyl chloride (18162-48-6) → 4-(tert-butyldimethylsilyloxy)-phenyl-acetonitrile (167263-57-2)

Conditions	Yield
In N,N-dimethyl-formamide	98%
With sodium chloride In water; N,N-dimethyl-formamide
With sodium chloride In water; N,N-dimethyl-formamide

4-cyanomethylphenol (14191-95-8) + tert-butylchlorodiphenylsilane (58479-61-1) → (4-{[tert-butyl(diphenyl)silyl]oxy}phenyl)acetonitrile (1173102-57-2)

Conditions	Yield
With 1H-imidazole In dichloromethane at 20℃;	98%

4-cyanomethylphenol (14191-95-8) + benzyl bromide (100-39-0) → 2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0)

Conditions	Yield
With potassium carbonate In acetone for 17h; Heating;	97%
With potassium carbonate In DMF (N,N-dimethyl-formamide) at 20℃;	96%
With potassium carbonate In N,N-dimethyl-formamide at 70℃; for 10 - 12h;	88%

4-cyanomethylphenol (14191-95-8) + allyl bromide (106-95-6) → 2-(4-(allyloxy)phenyl)acetonitrile (515163-31-2)

Conditions	Yield
In acetonitrile for 6h; Reflux; Inert atmosphere;	97%
With potassium carbonate In acetone at 20℃; for 24h;	85%
With potassium carbonate In acetone at 66℃; for 12h;

4-cyanomethylphenol (14191-95-8) + 4-bromo-benzaldehyde (1122-91-4) → (E)-3-(4-bromophenyl)-2-(4-hydroxyphenyl)acrylonitrile

Conditions	Yield
Stage #1: 4-cyanomethylphenol With potassium tert-butylate In ethanol for 0.5h; Stage #2: 4-bromo-benzaldehyde In ethanol at 20℃; for 3h;	97%

2-chloroethyl methyl ether (627-42-9) + 4-cyanomethylphenol (14191-95-8) → 4-(2-methoxyethoxy)-benzyl cyanide (352547-54-7)

Conditions	Yield
With potassium carbonate	96.8%

4-cyanomethylphenol (14191-95-8) + C16H11NO → C24H16N2O

Conditions	Yield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	96%

4-cyanomethylphenol (14191-95-8) + C16H10BrNO → C24H15BrN2O

Conditions	Yield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	96%

4-cyanomethylphenol (14191-95-8) + C17H13NO2 → C25H18N2O2

Conditions	Yield
With sodium methylate In methanol; ethanol at 20℃; for 0.166667h;	96%

4-cyanomethylphenol (14191-95-8) → 2-(4-hydroxy-3-nitrophenyl)acetonitrile

Conditions	Yield
With sulfuric acid; nitric acid In dichloromethane at 0℃;	96%

tert-amyl hydroperoxide (3425-61-4) + 4-cyanomethylphenol (14191-95-8) → C12H16O3

Conditions	Yield
With Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(IDA)3; potassium hydroxide In acetonitrile at 80℃; for 10h;	96%

1-bromo-hexane (111-25-1) + 4-cyanomethylphenol (14191-95-8) → 2-(4-(hexyloxy)phenyl)acetonitrile (61017-93-4)

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 4h;	95.5%
With potassium carbonate In acetonitrile for 3h; Reflux;	93%
Stage #1: 4-cyanomethylphenol With potassium carbonate In ethanol for 0.333333h; Stage #2: 1-bromo-hexane In ethanol at 50℃; for 5h;	88.7%

4-cyanomethylphenol (14191-95-8) + benzyl bromide (100-39-0) → [1(R)]-3-(aminomethyl)-3-[4-[(2,6-dimethyl-4-pyridinyl)methoxy]phenyl]-N-hydroxy-alpha-(2-methylpropyl)-2-oxo-1-pyrrolidineacetamide bis(trifluoroacetate) + 2-[4-(benzyloxy)phenyl]acetonitrile (838-96-0)

Conditions	Yield
With potassium carbonate In acetone	A n/a B 95%

4-cyanomethylphenol (14191-95-8) → tyramine hydrochloride (60-19-5)

Conditions	Yield
With hydrogenchloride; 1% Pd/C; hydrogen In ethanol; water under 2585.81 Torr; for 12h;	95%

tert.-butylhydroperoxide (75-91-2) + 4-cyanomethylphenol (14191-95-8) → tert-butyl 4-hydroxybenzoate (25804-49-3)

Conditions	Yield
With Zr6(μ3-O)4(μ3-OH)4(OH)6(H2O)6(IDA)3; potassium hydroxide In acetonitrile at 80℃; for 10h;	95%
In water; acetonitrile at 60℃; for 16h; Molecular sieve; Schlenk technique; Inert atmosphere;	72%

4-cyanomethylphenol (14191-95-8) + phenylboronic acid (98-80-6) → 2-(4-hydroxyphenyl)-1-phenylethan-1-one (6420-90-2)

Conditions	Yield
With trifluorormethanesulfonic acid; palladium diacetate; 2-(3,5-dimethyl-1H-pyrazol-1-yl)pyridine In water at 60℃; for 2h;	94%

4-cyanomethylphenol (14191-95-8) + benzyl bromide (100-39-0) → 4-benzyloxy-1-(α,α-dibenzyl)cyanomethylbenzene

Conditions	Yield
With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide for 18h; Heating;	93%

3,4-dihydro-2H-pyran (110-87-2) + 4-cyanomethylphenol (14191-95-8) → [4-(tetrahydro-2H-pyran-2-yloxy)phenyl]acetonitrile (19001-09-3)

Conditions	Yield
With toluene-4-sulfonic acid at 0℃; for 1.5h;	93%

4-cyanomethylphenol (14191-95-8) + 5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene (470474-31-8) → 13-(4-hydroxybenzyl)-15,16-bisnorlabda-8(17)-en-14-nitrile

Conditions	Yield
Stage #1: 4-cyanomethylphenol With sodium hydride In tetrahydrofuran for 1.5h; Reflux; Stage #2: 5-(2-bromo-ethyl)-1,1,4α-trimethyl-6-methylene-decahydro-naphthalene In tetrahydrofuran for 3h; Reflux;	93%

Upstream product

• 56401-28-6 [2-hydroxyimino-3-(4-hydroxyphenyl)]propionic acid 
• 108-24-7 acetic anhydride 
• 773837-37-9 sodium cyanide 
• 150-76-5 4-methoxy-phenol 
• 623-05-2 (4-hydroxyphenyl)methanol 
• 1252085-64-5 4-hydroxyphenylacetonitrile 4-O-β-D-glucopyranosyl(1->6)-β-D-glucopyranoside 
• 106-44-5 p-cresol 
• 19158-51-1 P-toluenesulfonyl cyanide 
• 35421-08-0 4-hydroxybenzyl chloride 
• 143-33-9 sodium cyanide 
• 104-47-2 p-methoxybenzylnitrile 
• 60-18-4 L-tyrosine 
• 3544-25-0 p-aminophenylacetonitrile 
• 17194-82-0 2-(4-hydroxyphenyl)acetamide 

Downstream Products

• 873411-89-3 4'-hydroxy-2,4,6-trimethoxy-deoxybenzoin 
• 141805-71-2 2-(4-hydroxy-phenyl)-acetimidic acid ethyl ester; hydrochloride 
• 101733-40-8 1,1,1-trichloro-2,2-bis-[2-(4-hydroxy-phenyl)-acetylamino]-ethane 
• 60982-68-5 (p-Heptoxyphenyl)acetonitril 
• 60982-69-6 (4-n-octyloxyphenyl)acetonitrile 
• 29277-73-4 1-(4'-cyanomethylphenoxy)-2-hydroxy-3-(isopropylamino)propane 
• 114497-66-4 2-[4-(Quinolin-2-yl-methoxy)phenyl]-acetonitrile 
• 90844-74-9 p-(2-Brom-ethoxy)-phenylacetonitril 
• 4919-33-9 4-ethoxyphenylacetic acid 
• 50690-52-3 (4-propoxy-phenyl)-acetonitrile 
• 34074-31-2 Bis-cyanomethyl-1,2-diphenoxyethane 
• 850143-24-7 2-(4-(hexadecyloxy)phenyl)acetonitrile 
• 80280-48-4 2-(4-(octadecyloxy)phenyl)acetonitrile 
• 884320-49-4 2-(4-(triisopropyl)silyloxyphenyl)acetonitrile 

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