628-13-7

Basic information

• Product Name: Pyridine hydrochloride
• Synonyms: PYRIDINIUM MONOCHLORIDE;PYRIDINIUM CHLORIDE;PYRIDINE HYDROCHLORIDE;PYRIDINE HCL;Pyridine hydrochloride, 97+%;Pyridinehydrochloride,98%;Pyridine hydrochloride, pure, 98%;PYRIDINE HYDROCHLORIDE PYRIDINE HYDROCHLORIDE
• CAS NO: 628-13-7
• Molecular Formula: C₅H₆N*Cl
• Molecular Weight: 115.56
• EINECS: 211-027-4
• Product Categories: Heterocyclic Compounds;Pyridinium Compounds;Heterocycle-Pyridine series
• Mol File: 628-13-7.mol
• Article Data: 138

Chemical Properties

• Melting Point: 145-147 °C(lit.)
• Boiling Point: 222-224 °C(lit.)
• Flash Point: 222-224°C
• Appearance: White to tan/Crystals
• Density: 1.1182 (rough estimate)
• Vapor Pressure: 22.8mmHg at 25°C
• Refractive Index: 1.5304 (estimate)
• Storage Temp.: Store below +30°C.
• Solubility: ethanol: soluble50mg/mL, clear, colorless to light yellow
• Water Solubility: 85 g/100 mL
• Sensitive: Hygroscopic
• Stability: Hygroscopic
• BRN: 3615340
• CAS DataBase Reference: Pyridine hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Pyridine hydrochloride(628-13-7)
• EPA Substance Registry System: Pyridine hydrochloride(628-13-7)

Safety Data

• Hazard Codes: Xn,Xi
• Statements: 20/21/22-36/37/38-22
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: UT4375000
• F: 3-10
• TSCA: Yes
• Hazardous Substances Data: 628-13-7(Hazardous Substances Data)

Usage

Chemical Properties

white to tan crystals

Uses

Different sources of media describe the Uses of 628-13-7 differently. You can refer to the following data:
1. Pyridine Hydrochloride is the hydrochloride salt of pyridine, a basic six-membered heterocyclic ring. Pyridine is a base structure present in many biologically active compounds like the vitamins niaci n and pyridoxal. Pyridine is used in dehalogenation reactions and can be used as a base in condensation reactions.
2. Pyridine Hydrochloride is the hydrochloride salt of pyridine, a basic six-membered heterocyclic ring. Pyridine is a base structure present in many biologically active compounds like the vitamins niacin and pyridoxal. Pyridine is used in dehalogenation reactions and can be used as a base in condensation reactions.

Purification Methods

Crystallise the salt from CHCl3/EtOAc and wash it with Et2O. It is hygroscopic.[Beilstein 20 H 185, 20 I 57, 20 II 103, 20 III/IV 2230, 20/5 V 180.]

InChI:InChI=1/C5H5N.ClH/c1-2-4-6-5-3-1;/h1-5H;1H

Synthetic route

pyridine (110-86-1) + tert-butylsulfinyl chloride (31562-43-3) → pyridine hydrochloride (628-13-7) + acetone (67-64-1) + pyridinium tert-butylsulfonate + tert-butyl alcohol (75-65-0)

Conditions	Yield
With tert.-butylhydroperoxide In chloroform at 20℃; for 2h; Further byproducts given;	A 100% B 20% C 40% D 55%

tert-butylsulfinyl chloride (31562-43-3) + tert-butyl hydrodisulfide (68409-52-9) → tert-butylsulfenic tert-butylsulfinic dithioanhydride (62383-66-8) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With pyridine In chloroform at 20℃; for 2h;	A 90% B 100%

z,z,z-octadeca-6,9,12-trienoyl chloride (54562-14-0) + glycerol (56-81-5) → pyridine hydrochloride (628-13-7) + tri-γ-linolenin (14465-68-0)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20 - 35℃;	A n/a B 96.3%
Stage #1: z,z,z-octadeca-6,9,12-trienoyl chloride; glycerol With pyridine In dichloromethane at 35℃; Stage #2: dmap In dichloromethane at 20℃; Product distribution / selectivity;	A n/a B 65%

pyridine (110-86-1) → pyridine hydrochloride (628-13-7) + N-sulfonic acid pyridinium chloride

Conditions	Yield
With chlorosulfonic acid In dichloromethane at 0℃; for 0.5h;	A n/a B 95%

pyridine (110-86-1) + 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8) + acetyl chloride (75-36-5) → 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-diacetate (946424-26-6) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With dmap In ethyl acetate at 60 - 65℃;	A 94% B n/a

ortho-toluoyl chloride (933-88-0) + adenosine (58-61-7) → pyridine hydrochloride (628-13-7) + N6,2',3',5'-tetra-O-toluoyladenosine (104579-36-4) + o-Methylbenzamid (527-85-5)

Conditions	Yield
With methanol; ammonia In pyridine at 0℃;	A n/a B 93% C n/a

pyridine (110-86-1) + (2Z,4R,5R)-3-amino-4,5-dimethyl-oct-2-enoic acid ethyl ester (866108-64-7) + acetyl chloride (75-36-5) → (2Z,4R,5R)-3-acetylamino-4,5-dimethyl-oct-2-enoic acid ethyl ester (866108-66-9) + pyridine hydrochloride (628-13-7)

Conditions	Yield
In dichloromethane at -20 - 0℃; for 2.5h;	A 93% B n/a

pyridine (110-86-1) + 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8) + phenylacetyl chloride (103-80-0) → 2-deoxy-2,2-difluoro-D-erythro-pentofuranos-1-ulose-3,5-bis(phenylacetate) (946424-25-5) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With dmap In ethyl acetate at 60 - 65℃;	A 92.9% B n/a

pyridine (110-86-1) → pyridine hydrochloride (628-13-7)

Conditions	Yield
With acetyl chloride In methanol; diethyl ether at 0℃; for 1h; Inert atmosphere;	92%
With chlorosulfonic acid In 1,2-dichloro-ethane at 25℃; Thermodynamic data; ΔH(formation of product);
With hydrogenchloride In 1,2-dichloro-ethane at 25℃; Thermodynamic data; ΔH(formation of product);

n-decanoyl chloride (112-13-0) + glycerol (56-81-5) → capric acid triglyceride (621-71-6) + pyridine hydrochloride (628-13-7)

Conditions	Yield
Stage #1: n-decanoyl chloride; glycerol With pyridine In dichloromethane at 20 - 35℃; for 0.0833333 - 0.25h; Stage #2: With dmap at 20℃;	A 86% B n/a

2-tert-butylmalonyl dichloride (78775-72-1) + 2-bromoethanol (540-51-2) → pyridine hydrochloride (628-13-7) + tert-Butylmalonsaeure-bis(2-bromethylester) (78775-97-0)

Conditions	Yield
With pyridine In benzene for 41h;	A n/a B 83%

1,2-dichlorotetramethylsilane (4342-61-4) → octamethyl-1,4-dioxa-2,3,5,6-tetrasilacyclohexane (17865-73-5) + pyridine hydrochloride (628-13-7) + NiCl2*4Py

Conditions	Yield
With pyridine; nickel dihydroxide In toluene; acetonitrile Heating;	A 69% B 70.6% C n/a

1,3-dihydroxyacetone dimer (62147-49-3) + n-decanoyl chloride (112-13-0) → 1,3-dicaproyloxypropan-2-one (73312-67-1) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20 - 30℃;	A 60% B n/a

1, 3-dicaprin (17598-93-5) + z,z,z-octadeca-6,9,12-trienoyl chloride (54562-14-0) → glycerol 1,3-didecanoate 2-octadecatri(6-Z, 9-Z, 12-Z)enoate (847019-77-6) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With pyridine; dmap In dichloromethane at 10 - 20℃;	A 56% B n/a

1, 3-dicaprin (17598-93-5) + arachidonoyl chloride (57303-04-5) → glycerol 1,3-didecanoate 2-eicosatetra-(5-Z, 8-Z, 11-Z, 14-Z)enoate + pyridine hydrochloride (628-13-7)

Conditions	Yield
With pyridine; dmap In dichloromethane at 10 - 20℃;	A 56% B n/a

pyridine (110-86-1) + 4-chloro-benzoyl chloride (122-01-0) + 2-deoxy-2,2-difluoro-1-carbonylribose (95058-77-8) → 2-deoxy-2,2-difluoro-D-erythro-pentofiranos-1-ulose-3,5-di(4-chlorobenzoate) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With dmap In ethyl acetate at 60 - 65℃; for 370h;	A 54.1% B n/a

1,3-diolein (2465-32-9, 98168-52-6) + z,z,z-octadeca-6,9,12-trienoyl chloride (54562-14-0) → pyridine hydrochloride (628-13-7) + 1,3-dioleoyl-2-dihomo-γ-linolenoyl glyceride

Conditions	Yield
With pyridine; dmap In dichloromethane at 10 - 20℃;	A n/a B 54%

arachidonoyl chloride (57303-04-5) + glycerol (56-81-5) → pyridine hydrochloride (628-13-7) + 1,2,3-tris[(cis,cis,cis,cis)-5,8,11,14-eicosatetraenoyl]glycerol (23314-57-0)

Conditions	Yield
With pyridine; dmap at 25 - 42℃; for 2h; Neat (no solvent);	A n/a B 43%

1,3-dihydroxyacetone dimer (62147-49-3) + (Z)-9-octadecenoyl chloride (112-77-6) → 2-oxopropane-1,3-diyl dioleate (24472-44-4) + pyridine hydrochloride (628-13-7)

Conditions	Yield
With pyridine; dmap In dichloromethane at 20℃;	A 27% B n/a

tetraethylammonium pentachloro(pyridine)iridate(IV) (118773-91-4) + dimethylsulfide (75-18-3) + ascorbic acid (50-81-7) → tetraethylammonium pentachloro(dimethylsulphide)iridate(IV) (118773-83-4) + pyridine hydrochloride (628-13-7)

Conditions

Yield

With HCl; chlorine In ethanol; dichloromethane Ir-compd. dissolved in warm ethanol, dropwise addn. of ascorbic acid in ethanol, addn. of ligand in CH2Cl2, refluxed for 1 h, ethanol evapd. in vac., dissolved in CH2Cl2, oxidised with chlorine, saturated with HCl, after 1 h purged with nitrogen; partioned with water, organic phase separated and dried over Na2SO4, reduced in vac., addn. of diethyl ether, left at -10°C, liquid decanted off, dried in vac.; elem. anal.;

A 20% B n/a

tetraethylammonium pentachloro(pyridine)iridate(IV) (118773-91-4) + dimethylselenide (593-79-3) + ascorbic acid (50-81-7) → tetraethylammonium pentachloro(dimethylselenide)iridate(IV) (118773-79-8) + pyridine hydrochloride (628-13-7)

Conditions

Yield

With HCl; chlorine In ethanol; dichloromethane Ir-compd. dissolved in warm ethanol, dropwise addn. of ascorbic acid in ethanol, addn. of ligand in CH2Cl2, refluxed for 1 h, ethanol evapd. in vac., dissolved in CH2Cl2, oxidised with chlorine, saturated with HCl, after 1 h purged with nitrogen; partioned with water, organic phase separated and dried over Na2SO4, reduced in vac., addn. of diethyl ether, left at -10°C, liquid decanted off, dried in vac.; elem. anal.;

A 20% B n/a

tetraethylammonium pentachloro(pyridine)iridate(IV) (118773-91-4) + ascorbic acid (50-81-7) → tetraethylammonium pentachloro(triphenylphosphine)iridate(IV) (118773-77-6) + pyridine hydrochloride (628-13-7)

Conditions

Yield

With P(C6H5)3; chlorine; HCl In ethanol; dichloromethane Ir-compd. dissolved in warm ethanol, dropwise addn. of ascorbic acid in ethanol, addn. of ligand in CH2Cl2, refluxed for 1 h, ethanol evapd. in vac., dissolved in CH2Cl2, oxidised with chlorine, saturated with HCl, after 1 h purged with nitrogen; partioned with water, organic phase separated and dried over Na2SO4, reduced in vac., addn. of diethyl ether, left at -10°C, liquid decanted off, dried in vac.; elem. anal.;

A 20% B n/a

tetraethylammonium pentachloro(pyridine)iridate(IV) (118773-91-4) + triphenyl-arsane (603-32-7) + ascorbic acid (50-81-7) → tetraethylammonium pentachloro(triphenylarsine)iridate(IV) (118773-89-0) + pyridine hydrochloride (628-13-7)

Conditions

Yield

With HCl; chlorine In ethanol; dichloromethane Ir-compd. dissolved in warm ethanol, dropwise addn. of ascorbic acid in ethanol, addn. of ligand in CH2Cl2, refluxed for 1 h, ethanol evapd. in vac., dissolved in CH2Cl2, oxidised with chlorine, saturated with HCl, after 1 h purged with nitrogen; partioned with water, organic phase separated and dried over Na2SO4, reduced in vac., addn. of diethyl ether, left at -10°C, liquid decanted off, dried in vac.; elem. anal.;

A 20% B n/a

tetraethylammonium pentachloro(pyridine)iridate(IV) (118773-91-4) + triphenylantimony (603-36-1) + ascorbic acid (50-81-7) → tetraethylammonium pentachloro(triphenylstibine)iridate(IV) (118773-85-6) + pyridine hydrochloride (628-13-7)

Conditions

Yield

With HCl; chlorine In ethanol; dichloromethane Ir-compd. dissolved in warm ethanol, dropwise addn. of ascorbic acid in ethanol, addn. of ligand in CH2Cl2, refluxed for 1 h, ethanol evapd. in vac., dissolved in CH2Cl2, oxidised with chlorine, saturated with HCl, after 1 h purged with nitrogen; partioned with water, organic phase separated and dried over Na2SO4, reduced in vac., addn. of diethyl ether, left at -10°C, liquid decanted off, dried in vac.; elem. anal.;

A 20% B n/a

4-isopropyl-borinine; compound with pyridine + pyridine hydrochloride (628-13-7) → C13H17BN(1+)*C5H5N*Cl(1-)

Conditions	Yield
In dichloromethane at 20℃; for 0.25h;	100%

5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine (930606-42-1) + pyridine hydrochloride (628-13-7) → 4-{[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]amino}quinazolin-5-ol (930606-35-2)

Conditions	Yield
Stage #1: 5-methoxy-N-[1-(pyridin-2-ylmethyl)-1H-indazol-5-yl]quinazolin-4-amine; pyridine hydrochloride In pyridine for 3h; Heating / reflux; Stage #2: With sodium hydrogencarbonate In water for 0.5h; Product distribution / selectivity;	100%

trimethylsilylimidovanadium(V)-trichloride (99589-88-5) + pyridine hydrochloride (628-13-7) → pyridinium-nitrido-trichlorovanadate(V)

Conditions	Yield
In toluene all manipulations under Ar; pyridinium salt added to soln. of V compd. with stirring, suspn. stirred for 12 h; filtered, washed with toluene, dried in vac.; elem. anal.;	98%

(N,N′-bis(2,4,6-trimethylphenyl)imidazole-2-ylidene)Pd(acac)Cl + pyridine hydrochloride (628-13-7) → [PdCl2{1,3-dimesitylimidazol-2-ylidene}(pyridine)]

Conditions	Yield
With air In 1,4-dioxane at 20℃;	98%
In 1,4-dioxane at 20℃; for 24h; Inert atmosphere;	70 mg

pyridine hydrochloride (628-13-7) → pyridine hydroiodide (18820-83-2)

Conditions	Yield
With methyl iodide In acetonitrile Heating;	97%

(1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene)Pd(acetylacetonato)Cl + pyridine hydrochloride (628-13-7) → SIPr-PdCl2-Py

Conditions	Yield
at 20℃;	97%

C32H45ClN2O2Pd*CHCl3 + pyridine hydrochloride (628-13-7) → trans-[1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene]PdCl2(NC5H5)

Conditions	Yield
With air In 1,4-dioxane at 20℃;	97%

pyridine (110-86-1) + Gallium trichloride (13450-90-3) + pyridine hydrochloride (628-13-7) → pyridine-pyridinium tetrachlorogallate(III) (72794-64-0)

Conditions	Yield
In pyridine (N2); soln. of GaCl3 in pyridine and soln. of C5H5NHCl in pyridine were combined; after 1 h pyridine removed (vac.); residue crystd. (toluene); elem. anal.;	95%

[(IPr)Pd(acac)Cl] + pyridine hydrochloride (628-13-7) → {1,3-bis[2,6-bis(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}dichloro(pyridine)palladium

Conditions	Yield
at 20℃;	95%

[(IPr)Pd(acac)Cl] + pyridine hydrochloride (628-13-7) → {1,3-bis[2,6-di(propan-2-yl)phenyl]-1,3-dihydro-2H-imidazol-2-ylidene}(dichloro)(pyridine)palladium

Conditions	Yield
With air In 1,4-dioxane at 20℃;	95%

tris(2,6-dimethylphenylimino)methylrhenium(VII) (134695-26-4) + pyridine hydrochloride (628-13-7) → dichlorobis(2,6-dimethylphenylimido)methyl(pyridine)rhenium(VII)

Conditions	Yield
In dichloromethane addn. of educts; stirred for 1 h at room temp.;; solvent concd. in vacuo; mixed with hexane; elem. anal.;;	94%

{Re(NC6H3(CH(CH3)2)2)3}(1-)*{Na(C4H8O)2}(1+)={Re(NC6H3(CH(CH3)2)2)3}{Na(C4H8O)2} + pyridine hydrochloride (628-13-7) + benzene (71-43-2) → {Re(NC6H3(CH(CH3)2)2)(C5H5N)2Cl3}*C6H6

Conditions	Yield
In tetrahydrofuran; pyridine byproducts: H2NC6H3(CH(CH3)2)2, NaCl; addn. of 22.8 mmol of the Na(THF)2 salt to a stirred slurry of 105 mmol (C5H5NH)Cl in 50 ml THF / 200 ml C5H5N, concn. to 30 ml after 10 min., addn. of 300 ml pentane, washing, drying and refluxing with 150 ml C6H6, 5 days, concn. and addn. of pentane;; drying in vacuum; detn. by elem. anal., (1)H-NMR- and (13)C-NMR spectroscopy;;	94%

pentacyanocyclopentadienyl anion sodium salt + pyridine hydrochloride (628-13-7) → pyridium pentacyanocyclopentadienide

Conditions	Yield
In water	93%

palladium(II) hexafluoroacetylacetonate + pyridine hydrochloride (628-13-7) → chloro(1,1,1,5,5,5-hexafluoro-2,4-pentanedionato)(pyridine)palladium(II)

Conditions	Yield
In methanol; dichloromethane CH2Cl2 son. of complex was added to MeOH soln. of Py*HCl; standing 1 d at room temp.; treatment with hexane. cooling;	92%

Upstream product

• 110-86-1 pyridine 
• 60-29-7 diethyl ether 
• 6169-06-8 (S)-2-Octanol 
• 74-90-8 hydrogen cyanide 
• 75-36-5 acetyl chloride 
• 4342-61-4 1,2-dichlorotetramethylsilane 
• 54562-14-0 z,z,z-octadeca-6,9,12-trienoyl chloride 
• 56-81-5 glycerol 
• 17598-93-5 1, 3-dicaprin 
• 2465-32-9 1,3-diolein 
• 126104-52-7 di-homo-gamma-linolenyl chloride 
• 1122-58-3 dmap 
• 79-06-1 2-propenamide 
• 75760-11-1 (S)-methyl 3-amino-2-(((benzyloxy)carbonyl)amino)propanoate 

Downstream Products

• 110-56-5 1,4-dichlorobutane 
• 842-07-9 Sudan I 
• 860567-48-2 2-chloro-1-(2-nitro-phenyl)-ethanol 
• 53993-41-2 (Z)-2-Chloro-but-2-enoic acid 
• 2116-65-6 4-benzyl pyridine 
• 101-82-6 2-Benzylpyridine 
• 102-02-3 1-phenylbiguanide 
• 71-36-3 butan-1-ol 
• 527-54-8 3,4,5-trimethylphenol 
• 53-16-7 Estrone 
• 16604-76-5 thiophosphoric acid S-ethyl ester-O,O'-bis-(4-nitro-phenyl ester) 
• 109-69-3 n-Butyl chloride 
• 1857-53-0 4-(5-chloro-benzothiazol-2-ylmethyl)-phenol 
• 60-35-5 acetamide 

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