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2-(2-Hydroxyethyl)pyridine

HCID 7675
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Basic informationOverviewNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
103-74-2
Standard SMILES
OCCc1ccccn1
InChIKey
BXGYBSJAZFGIPX-UHFFFAOYSA-N
Molecular formula
C7H9NO
Average molar mass
123.15 g/mol
Monoisotopic mass
123.06841391

Overview

2-Pyridylethanol is a member of pyridines.

Names & identifiers

Preferred name
2-(2-Hydroxyethyl)pyridine
IUPAC
2-pyridin-2-ylethanol
English name
2-(2-Hydroxyethyl)pyridine
Molecular formula
C7H9NO
Molecular weight
123.15

Names & synonyms

2-(2-Hydroxyethyl)pyridineRefChem:893582-PYRIDINEETHANOL103-74-22-(2-Pyridyl)ethanolPyridine-2-ethanol2-(Pyridin-2-Yl)Ethan-1-Ol2-pyridin-2-ylethanol2-Pyridylethanol2-(Pyridin-2-yl)ethanolBetahistine EP Impurity B2-(beta-Hydroxyethyl)pyridine
Show more names
2-ETHANOLPYRIDINEBetahistine Impurity B2-Pyridinethanol2-Pyridineethonl2-Pyridien ethanolP-nitrochlorobenzen
Pyridine, 2-(2-hydroxyethyl)-2-(2-Pyridinyl)ethanolUNII-4G94J9B8JRMFCD000063644G94J9B8JRDTXSID2044767NSC-21442-(.ALPHA.-PYRIDYL)ETHANOL

Database identifiers

CAS
103-74-2
PubChem CID
7675
DTXSID
DTXSID2044767
ChEMBL
CHEMBL3186451
ChEBI
CHEBI:230061
UNII
4G94J9B8JR
EC Number
203-140-2
Nikkaji
J28.225A

Properties

Computed structural propertiesFilling in

XLogP
0.1
Topological polar surface area
33.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
2
Rotatable bonds
2
Heavy atoms
9
Formal charge
0
Complexity
75.3

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Pyridines
LogP · 2 items

log Kow= 0.12

0.12

Density1.091 @ 25 °C/0 °C
SolubilityVery soluble in alcohol, chloroform; slightly soluble in ether
Boiling Point190 °C @ 200 mm Hg; 170 °C @ 100 mm Hg
Melting Point-7.8 °C
Vapor Pressure0.0000703 [mmHg]
Refractive IndexIndex of refraction: 1.5366 @ 20 °C/D
Physical Description · 2 items

Liquid

Hygroscopic; [HSDB] Liquid; [MSDSonline]

Dissociation ConstantspKa = 5.31 (conjugate acid)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H315 (50.5%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 91 reports by companies from 8 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 2 items

2-Pyridineethanol is listed on the EPA's Chemical Data Reporting (CDR) system. Manufacturers and importers of 2-Pyridineethanol are required to report information about their production and use of this chemical to the EPA under the Toxic Substances Control Act (TSCA). (40 eCFR Part 711)

Status: Active Update: 26-09-2013 https://echa.europa.eu/registration-dossier/-/registered-dossier/13451

Hazards SummaryEmergency treatment: Pyridine; Pyridine is an irritant that causes CNS depression after ingestion of 1/2 cup or inhalation of 6-12 ppm; It can cause liver and kidney injury; [HSDB] An irritant; [MSDSonline] See Pyridine.
Hazard Classes and CategoriesSkin Irrit. 2 (50.5%)
Skin, Eye, and Respiratory IrritationsPyridine and its derivatives cause local irritation on contact with the skin, mucous membranes and cornea. /Pyridine and its derivatives/

Safety & protection

Disposal Methods · 1 item

Chemistry & industry

Pharmacology

Absorption, Distribution and Excretion · 1 item

PYRIDINE & ITS ALKYL DERIVATIVES ARE ABSORBED FROM GI TRACT, INTRAPERITONEAL CAVITY & LUNGS. PERITONEAL ABSORPTION IS APPARENTLY ONLY SLIGHTLY MORE RAPID & COMPLETE THAN GI ABSORPTION ... IN GENERAL THE BASES ARE RAPIDLY ABSORBED THROUGH INTACT SKIN. /ALKYL DERIVATIVES OF PYRIDINE/

Uses & manufacturing

Uses · 2 items

Used in the manufacturing of vinyl pyridines, thioridazine (psychotropic agent), and tiquizium bromide (antispasmodic); [HSDB]

Manufacture of vinyl pyridines; production of psychotropic agent, thioridazine, and the antispasmodic, tiquizium bromide.

U.S. Production2023: 1,000,000 - <5,000,000 lb
Industry UsesIntermediate
Methods of ManufacturingCondensation of 2- or 4-methylpyridine or 5-ethyl-2-methylpyridine with formaldehyde occurs on heating to yield ... 2-(2-hydroxyethyl)pyridine.
General Manufacturing Information · 2 items

All Other Basic Organic Chemical Manufacturing

2-Pyridineethanol: ACTIVE

Applications · 3 items

Uses2-Pyridineethanol is a metabolite of the anti-vertigo drug Betahistine (B324000).

Uses2-(2-Hydroxyethyl)pyridine is a metabolite of the anti-vertigo drug Betahistine. It acts as a reagent for protection of the 5'-phosphate of nucleotides as 2-pyridylethyl (Pet) esters. It is used for carboxyl protection of amino acids. It is also used to cleave such groups as Boc and Fmoc, and also to hydrogenolysis. It was used to prepare mononuclear nickel(II) acetate.

Related reactions

87 records
New reaction record
HRID 65555 reaction equation
HRID 65555As reactantuspto-grants-1978_12
HRID 70368 reaction equation
HRID 70368As reactantuspto-grants-2014_09
HRID 103555 reaction equation
HRID 103555As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 116745 reaction equation
HRID 116745As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 123128 reaction equation
HRID 123128As reactantTraining data from https://doi.org/10.1039/C8SC04228D (2/10)
HRID 142293 reaction equation
HRID 142293As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 146145 reaction equation
HRID 146145As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
HRID 147423 reaction equation
HRID 147423As reactantTraining data from https://doi.org/10.1039/C8SC04228D (9/10)
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Compound notes

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Collision Cross Section
120.7 Ų [M+H]+ [CCS Type: DT; Buffer gas: N2; Ionization: APCI+; Dataset: TOXCAST; Source Identifier: DTXSID2044767]
Other Experimental PropertiesHYGROSCOPIC

Physicochemical properties

Melting point
-8 · -8--7°C
Boiling point
114 · 114-116 °C/9 mmHg (lit.)
Density
1.093 g/mL · 1.093 g/mL at 25 °C (lit.)
vapor pressure
1.16 · 1.16-14.1Pa at 25℃
refractive index
20 · n20/D 1.537(lit.)
Flash point
199 °F · 199 °F
storage temp.
Inert atmosphere,Room Temperature
solubility
Soluble in Chloroform (Slightly), Methanol (Slightly).
form
Liquid
pka
14.49 · 14.49±0.10(Predicted)
color
Clear yellow to brown
PH
8 · 8-9 (100g/l, H2O, 20℃)
Water Solubility
soluble
Sensitive
Hygroscopic
BRN
111205 · 111205
Henry's Law Constant
6.6 · 6.6×104 mol/(m3Pa) at 25℃, HSDB (2015)
InChI
1S/C7H9NO/c9-6-4-7-3-1-2-5-8-7/h1-3,5,9H,4,6H2
InChIKey
BXGYBSJAZFGIPX-UHFFFAOYSA-N
SMILES
OCCc1ccccn1
LogP
0.38 · 0.38
CAS DataBase Reference
103 · 103-74-2(CAS DataBase Reference)
EWG's Food Scores
1 · 1
FDA UNII
4 G94J9B8JR · 4G94J9B8JR
NIST Chemistry Reference
2 · 2-Pyridineethanol(103-74-2)
EPA Substance Registry System
2 · 2-Pyridineethanol (103-74-2)
UNSPSC Code
12352100 · 12352100
NACRES
22 · NA.22
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
319 · H319
Precautionary statements
264 · P264-P280-P305+P351+P338-P337+P313
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes
Xi
Risk Statements
36 · 36/37/38
Safety Statements
26 · 26-36-24/25
WGK Germany
2 · 2
RTECS
2970450 · UT2970450
F
3 · 3
TSCA
TSCA listed
HS Code
29333999 · 29333999
Storage Class
10 · 10 - Combustible liquids
Hazard Classifications
2 · Eye Irrit. 2
Hazardous Substances Data
103 · 103-74-2(Hazardous Substances Data)
REACH Registrations
Active

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Preventive Measures · 1 item

SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.

Personal Protective Equipment (PPE) · 3 items

... WORKERS SHOULD BE PROVIDED WITH PERSONAL PROTECTIVE EQUIPMENT. A CHARCOAL GAS-MASK CANISTER RESPIRATOR HAS BEEN ... EFFECTIVE ... /PYRIDINE/

RUBBER & PLASTIC GLOVES SHOULD NOT BE RELIED UPON TO PREVENT SKIN CONTACT BECAUSE ... MANY ... /PYRIDINE/ DERIV PENETRATE THESE MATERIALS. /PYRIDINE/

Depending on the extent of possible contact, workers should be provided with personal protective equipment. A charcoal gas mask canister respirator has been found to be effective against a 2% pyridine concentration at 30 l/min for 1 hr. Rubber and plastic gloves should not be relied upon to prevent skin contact because pyridine and many of its derivatives penetrate these materials ... . /Pyridine, homologs, and derivatives/

Toxicology

Environmental Fate · 3 items

TERRESTRIAL FATE: Based on a classification scheme(1), a Koc value of 28(SRC), determined from a log Kow of 0.12(2) and a regression-derived equation(3), indicates that 2-pyridineethanol is expected to have very high mobility in soil(SRC). Volatilization of 2-pyridineethanol from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC). 2-Pyridineethanol is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 7.0X10-5 mm Hg(SRC), determined from a fragment constant method(4).

AQUATIC FATE: Based on a classification scheme(1), an estimated Koc value of 28(SRC), determined from a log Kow of 0.12(2) and a regression-derived equation(3), indicates that 2-pyridineethanol is not expected to adsorb to suspended solids and sediment(SRC). Volatilization from water surfaces is not expected(3) based upon an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole(SRC). According to a classification scheme(4), an estimated BCF of 3(SRC), from its log Kow(2) and a regression-derived equation(5), suggests the potential for bioconcentration in aquatic organisms is low(SRC).

ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), 2-pyridineethanol, which has an estimated vapor pressure of 7.0X10-5 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), will exist in both the vapor and particulate phases in the ambient atmosphere(SRC). Vapor-phase 2-pyridineethanol is degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals(SRC); the half-life for this reaction in air is estimated to be 2.6 days(SRC), calculated from its rate constant of 6.2X10-12 cu cm/molecule-sec at 25 °C(SRC) that was derived using a structure estimation method(3). Particulate-phase 2-pyridineethanol may be removed from the air by wet and dry deposition(SRC).

Adverse EffectsNeurotoxin - Other CNS neurotoxin
Soil Adsorption/Mobility · 1 item

The Koc of 2-pyridineethanol is estimated as 28(SRC), using a log Kow of 0.12(1) and a regression-derived equation(2). According to a classification scheme(3), this estimated Koc value suggests that 2-pyridineethanol is expected to have very high mobility in soil(SRC).

Fish/Seafood Concentrations2-Pyridineethanol was detected in adult Lake trout (Salvelinus namaycush) and/or walleye (Stizostediion v. vitreum) collected from Lake St Clair(1).
Artificial Pollution Sources2-Pyridineethanol's production and use in the manufacture of vinyl pyridines(1) may result in its release to the environment through various waste streams(SRC).
Environmental Bioconcentration · 1 item

An estimated BCF of 3 was calculated for 2-pyridineethanol(SRC), using a log Kow of 0.12(1) and a regression-derived equation(2). According to a classification scheme(3), this BCF suggests the potential for bioconcentration in aquatic organisms is low(SRC).

Volatilization from Water/Soil · 1 item

The Henry's Law constant for 2-pyridine ethanol is estimated as 1.5x10-10 atm-cu m/mole(SRC) using a fragment constant estimation method(1). This Henry's Law constant indicates that 2-pyridineethanol is expected to be essentially nonvolatile from water surfaces(2). 2-Pyridineethanol is not expected to volatilize from dry soil surfaces based upon an estimated vapor pressure of 7.0X10-5 mm Hg(SRC).

Environmental Abiotic Degradation · 1 item

The rate constant for the vapor-phase reaction of 2-pyridineethanol with photochemically-produced hydroxyl radicals has been estimated as 6.2x10-12 cu cm/molecule-sec at 25 °C(SRC) using a structure estimation method(1). This corresponds to an atmospheric half-life of about 2.6 days at an atmospheric concentration of 5X10+5 hydroxyl radicals per cu cm(1). 2-Pyridineethanol is not expected to undergo hydrolysis in the environment due to the lack of hydrolyzable functional groups(2). Pyridine has a weak absorption band that extends into the environmental UV spectrum, which suggests that direct photolysis is not likely to be an important fate process for 2-pyridineethanol (SRC).

Probable Routes of Human ExposureOccupational exposure to 2-pyridineethanol may occur by dermal contact with this compound at workplaces where 2-pyridineethanol is produced or used. (SRC)
Environmental Water ConcentrationsSURFACE WATER: 2-Pyridineethanol was detected in water sampled from the central basin of Lake Ontario(1).
Environmental Fate/Exposure Summary · 1 item

2-Pyridineethanol's production and use in the manufacture of vinyl pyridines may result in its release to the environment through various waste streams. If released to air, an estimated vapor pressure of 7.0X10-5 mm Hg at 25 °C indicates 2-pyridineethanol will exist in both the vapor and particulate phases in the ambient atmosphere. Vapor-phase 2-pyridineethanol will be degraded in the atmosphere by reaction with photochemically-produced hydroxyl radicals; the half-life for this reaction in air is estimated to be 2.6 days. Particulate-phase 2-pyridineethanol will be removed from the atmosphere by wet and dry deposition. If released to soil, 2-pyridineethanol is expected to have very high mobility based upon an estimated Koc of 28. Volatilization from moist soil surfaces is not expected to be an important fate process based upon an estimated Henry's Law constant of 1.5X10-10 atm-cu m/mole. If released into water, 2-pyridineethanol is not expected to adsorb to suspended solids and sediment based upon the estimated Koc. Volatilization from water surfaces is not expected to be an important fate process based upon this compound's estimated Henry's Law constant. An estimated BCF of 3 suggests the potential for bioconcentration in aquatic organisms is low. Hydrolysis is not expected to occur due to the lack of hydrolyzable functional groups. Occupational exposure to 2-pyridineethanol may occur by dermal contact with this compound at workplaces where 2-pyridineethanol is produced or used. (SRC)

Antidote and Emergency Treatment · 2 items

/SRP:/ Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if necessary. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool. Administer activated charcoal ... . /Aromatic hydrocarbons and related compounds/

/SRP:/ Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious or in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias if necessary ... Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Aromatic hydrocarbons and related compounds/

Safety data

F
3
PPE
Eyeshields, Gloves, type ABEK (EN14387) respirator filter
wgk
2
tsca
TSCA listed
rtecs
UT2970450
hs_code
29333999
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26-36-24/25
Storage Class
10 - Combustible liquids
Hazard statements
H319
REACH Registrations
Active
Hazard Classifications
Eye Irrit. 2
Precautionary statements
P264-P280-P305+P351+P338-P337+P313
Hazardous Substances Data
103-74-2(Hazardous Substances Data)

General Description2-(2-pyridyl)ethanol derivatives react with the aryl and alkenyl chlorides (palladium-catalyzed reactions) that result in the substitution of the chloro moieties with a 2-pyridylmethyl group.

Upstream & downstream products

Upstream raw materials

2- (2- hydroxyethyl) pyridine2-(Chloromethyl)pyridineFormaldehyde1,2-DibromoethaneTetrahydrofuranZINCChlorotrimethylsilane

Downstream products

Betahistine2-Vinylpyridine2-Piperidineethanol2-(2-Bromo-ethyl)-pyridine hydrobromide2-Picolinic acid2-Pyridin-2-ylethyl acetateBetahistine dihydrochloride2-Pyridineethanamine, N-(1-methylethyl)-Methanesulfonate-2-pyridineethanol ester2-(1-oxidopyridin-1-ium-2-yl)ethanol