CAS 768-66-1 2,2,6,6-Tetramethylpiperidine (HCID 13035)

Names & identifiers

Preferred name: 2,2,6,6-Tetramethylpiperidine
IUPAC: 2,2,6,6-tetramethylpiperidine
English name: 2,2,6,6-Tetramethylpiperidine
Molecular formula: C9H19N
Molecular weight: 141.25

Names & synonyms

2,2,6,6-Tetramethylpiperidine768-66-1NorpempidinePIPERIDINE, 2,2,6,6-TETRAMETHYL-2,2,6,6-TETRAMETHYL PIPERIDINEMFCD00005985HTMP2,2,6,6-tetramethyl-piperidine44N9S1YCFMNSC-1028382,2,6,6-TetramethylpeperidineEINECS 212-199-3

Show more names

TETRAMETHYLPIPERIDINE2,2,6,6-TetramethyL2,2,6,6-Teteamethyl-piperidine6-TetraMethylpiperidine2,2,6,6-Tetramethylpiperidine(Tmp)2,2,62,2,6,6-TetramethylpMedetomidine Impurity 100

UNII-44N9S1YCFMNSC 1028382,2,6,6 Tetramethyl piperidineNSC102838SCHEMBL151002,6,6-TetramethylpiperidineSCHEMBL146951SCHEMBL210605

Database identifiers

CAS: 768-66-1
PubChem CID: 13035
DTXSID: DTXSID0061113
ChEMBL: CHEMBL2448812
UNII: 44N9S1YCFM
EC Number: 212-199-3
Nikkaji: J1.732I

Properties

Computed structural properties

XLogP: 2.1
Topological polar surface area: 12 Å²
Hydrogen bond donors: 1
Hydrogen bond acceptors: 1
Rotatable bonds: 0
Heavy atoms: 10
Formal charge: 0
Complexity: 111

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Amines, Cyclic

SpringerMaterials PropertiesChemical shift

Vapor Pressure0.98 [mmHg]

Physical DescriptionLight yellow liquid; [Sigma-Aldrich MSDS]

Dissociation Constants11.1

Physicochemical properties

Melting point: -59 °C · -59°C
Boiling point: 152 °C · 152 °C (lit.)
Density: 0.837 g/mL · 0.837 g/mL at 25 °C (lit.)
vapor pressure: 14 hPa · 14 hPa (39 °C)
refractive index: 20 · n20/D 1.445(lit.)
Flash point: 76 °F · 76 °F
storage temp.: 30 °C · Store below +30°C.
solubility: MISCIBLE
pka: 11.07 · 11.07(at 25℃)
form: Liquid
Specific Gravity: 0.837 · 0.837
color: Clear colorless to yellow
Water Solubility: MISCIBLE
Sensitive: Air Sensitive
BRN: 103296 · 103296
InChI: 1S/C9H19N/c1-8(2)6-5-7-9(3,4)10-8/h10H,5-7H2,1-4H3
InChIKey: RKMGAJGJIURJSJ-UHFFFAOYSA-N
SMILES: CC1(C)CCCC(C)(C)N1
CAS DataBase Reference: 768 · 768-66-1(CAS DataBase Reference)
EWG's Food Scores: 1 · 1
FDA UNII: 44 N9S1YCFM · 44N9S1YCFM
NIST Chemistry Reference: 2 · Piperidine, 2,2,6,6-tetramethyl-(768-66-1)
EPA Substance Registry System: 2 · Piperidine, 2,2,6,6-tetramethyl- (768-66-1)
UNSPSC Code: 12352005 · 12352005
NACRES: 22 · NA.22
Symbol(GHS): 2 · GHS02,GHS05,GHS07
Signal word: Danger
Hazard statements: 226 · H226-H290-H302-H314
Precautionary statements: 210 · P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338
target organs: Respiratory system
PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
Hazard Codes: Xn,F,C
Risk Statements: 10 · 10-22-36/37/38
Safety Statements: 26 · 26-37/39-16
RIDADR: 1992 · UN 1992 3/PG 3
WGK Germany: 2 · 2
RTECS: 4220000 · TN4220000
Autoignition Temperature: 290 °C · 290 °C
TSCA: TSCA listed
HazardClass: 3 · 3
PackingGroup: III
HS Code: 29333999 · 29333999
Storage Class: 3 · 3 - Flammable liquids
Hazard Classifications: 4 OralEye · Acute Tox. 4 OralEye Dam. 1Flam. Liq. 3Met. Corr. 1Skin Corr. 1ASTOT SE 3
Toxicity: 50 orally · LD50 orally in Rabbit: 500 mg/kg
REACH Registrations: Active
Limited Quantities: 5 L · 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)

Safety & regulation

GHS classification

GHS Classification · 4 items

Danger

H226 (97.1%): Flammable liquid and vapor [Warning Flammable liquids]

P210, P233, P240, P241, P242, P243, P260, P261, P264, P264+P265, P270, P271, P280, P301+P316, P301+P317, P301+P330+P331, P302+P352, P302+P361+P354, P303+P361+P353, P304+P340, P305+P351+P338, P305+P354+P338, P316, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P363, P370+P378, P403+P233, P403+P235, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 102 reports by companies from 23 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Regulatory Information · 3 items

Chemical: Piperidine, 2,2,6,6-tetramethyl-

Status: Active Update: 11-05-2017 https://echa.europa.eu/registration-dossier/-/registered-dossier/19475

2,2,6,6-Tetramethylpiperidine: Does not have an individual approval but may be used under an appropriate group standard

Hazards Summary · 1 item

Rats demonstrated effects possibly indicative of neurotoxicity in all test groups of acute inhalation study and high dose group (500 mg/kg) of acute oral study; [EPA - TSCATS] A skin and strong eye irritant; Toxic by ingestion; [Sigma-Aldrich MSDS] See Piperidine.

Hazard Classes and CategoriesFlam. Liq. 3 (97.1%)

Toxicology

Adverse EffectsNeurotoxin - Other CNS neurotoxin

Toxicity DataLC50 (rat) = 4,550 mg/m3/4hr

Safety data

PPE: Eyeshields, Faceshields, Gloves, type ABEK (EN14387) respirator filter
wgk: 2
tsca: TSCA listed
rtecs: TN4220000
ridadr: UN 1992 3/PG 3
hs_code: 29333999
Toxicity: LD50 orally in Rabbit: 500 mg/kg
risk_code: 10-22-36/37/38
Signal word: Danger
Symbol(GHS): GHS02,GHS05,GHS07
hazard_code: Xn,F,C
safety_code: 26-37/39-16
hazard_class: 3
Storage Class: 3 - Flammable liquids
packing_group: III
target organs: Respiratory system
Hazard statements: H226-H290-H302-H314
Limited Quantities: 5.0 L (1.3 gallons) (liquid)
Excepted Quantities: Max Inner Pack (30g or 30ml) and Max Outer Pack (1Kg or 1L)
REACH Registrations: Active
Hazard Classifications: Acute Tox. 4 OralEye Dam. 1Flam. Liq. 3Met. Corr. 1Skin Corr. 1ASTOT SE 3
Autoignition Temperature: 290 °C
Precautionary statements: P210-P233-P280-P301+P312-P303+P361+P353-P305+P351+P338

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationPiperidine, 2,2,6,6-tetramethyl-: ACTIVE

Applications · 3 items

Uses2,2,6,6-Tetramethylpiperidine is a hindered base used to prepare metallo-amide bases and selective generation of silylketene acetals. It is used in the preparation of hibarimicinone, (Z)-silylketene acetal and 4-substituted quinazoline. It acts as a precursor to Lithium tetramethylpiperidide and (2,2,6,6-Tetramethylpiperidin-1-yl)oxyl radical.

Uses2,2,6,6-Tetramethylpiperidine is used in the syntheses of HMP-Y1, Hibarimicinone and HMP-P1, tyrosine kinase inhibitors.

UsesThe lithium amide has been used to efficiently ortho deprotonate pyridine-3-carboxamides.

Preparation methods

PreparationMany routes for the synthesis of TMP have been reported. One method starts with a conjugate addition reaction of ammonia to phorone. The intermediate triacetone amine is then reduced in a Wolff-Kishner reaction.

Upstream & downstream products

Downstream products

2-Methoxy-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile 5-Fluoro-2-picolinic acid 5-Formyl-2,4-dimethoxypyrimidine 3-Bromo-2-((cyclopropylamino)methyl)benzaldehyde (E)-5-(2-Carboxyvinyl)-2,4-dimethoxypyrimidine 3-Cyanopyridin-4-ylboronic acid 5-(Trifluoromethyl)-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile 2-Chloro-6-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile 2-Cyanopyridin-3-ylboronic acid 3-Methoxy-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile 2-(3-Methoxyphenyl)cyclohexanone 4-(Trifluoromethyl)-2-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)benzonitrile

Suppliers100 total

梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]

衢州润东化工有限公司0570-8789886 18892685668 · [email protected]

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]

INTATRADE GmbH+49 3493/605464 · [email protected]

爱斯特（成都）生物制药股份有限公司+86-28-85122536 85324413 · [email protected]

Related reactions

658 records

New reaction record

HRID 12278As reactantuspto-grants-2010_06

HRID 20033As reactantuspto-grants-2010_06

HRID 20052As reactantuspto-grants-2010_06

HRID 22643As reactantuspto-grants-2005_02

HRID 34485As reactantuspto-grants-1988_08

HRID 38321As reactantuspto-grants-2013_09

HRID 38374As reactantuspto-grants-2013_09

HRID 42718As reactantuspto-grants-2013_09

Compound notes

Loading…

Basic information